bis(4-tert-butylphenyl)aminoxyl radical | 34549-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(4-tert-butylphenyl)aminoxyl radical
• 英文别名: bis(4-tert-butylphenyl)amine-N-oxyl radical；4,4'-di-tertbutyldiphenyl nitroxide；4,4′-di(tert-butyl phenyl)nitroxide；bis(4-tert-butylphenyl)amine-N-oxyl；4,4-di-tert-butyl-diphenylnitroxide radical；Bis(4-tert-butylphenyl)nitroxid；p-Di-tert.-butylphenyl-nitroxid
• CAS: 34549-00-3
• 化学式: C₂₀H₂₆NO
• 分子量: 296.433
• InChiKey: XSJOKDYRHPIXSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  4.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  bis(4-tert-butylphenyl)aminoxyl radical 在 铁粉 、 溶剂黄146 作用下， 反应 3.17h， 生成 二(4-叔丁基苯基)胺
  参考文献：
  名称：

  具有三重态基态的稳定的二芳基二氧杂双自由基。

  摘要：

  一氧化二氮自由基，第一个分离出的二芳基硝基氧自由基，在室温下处于稳定状态，并具有三重态基态和强铁磁耦合。

  DOI：

  10.1039/b909741d
• 作为产物：
  描述：

  二(4-叔丁基苯基)胺 在 间氯过氧苯甲酸 作用下， 以 氘代氯仿 为溶剂， 反应 0.5h， 以74%的产率得到bis(4-tert-butylphenyl)aminoxyl radical
  参考文献：
  名称：

  二芳基氮氧化物双自由基：二芳基胺低温氧化成氮氧化物

  摘要：

  开发了一种低温方法，在低温下用 DMDO 氧化仲二芳基胺的过程通过磁共振波谱（EPR 和 NMR）监测，并通过超导量子干涉装置 (SQUID) 进行磁性研究，用于制备第一个基于间亚苯基的二芳基氮氧化物双自由基。EPR 光谱和磁性研究 (SQUID) 表明二氯甲烷基质中的双自由基主要采用反构象 (2A-anti) 并具有三重基态。构象受限的氮杂[1 4]元环芳的类似氧化实验为形成少量相应的二芳基氮氧化物双自由基提供了证据。两种二芳基氮氧化物双自由基只能在低温（-80 摄氏度及以下）下检测到。

  DOI：

  10.1021/ja8016335

文献信息

• The exchange reaction of hydrogen atoms in the system sterically hindered hydroxylamine-nitroxyl radical
  作者：A. D. Malievskii、S. V. Koroteev

  DOI：10.1007/bf02495549

  日期：1998.7

  direct and reverse exchange reactions of the hydrogen atom in the system sterically-hindered nitroxyl radical-hydroxylamine of the quinoline, imidazoline, pyrrolidine, and piperidine series as well as diarylhydroxylamine were determined. A scale of the reductive abilities of the hydrolamines was established. A low value of the isotope effect is typical of the reactions of hydrogen exchange in the systems

  测定了喹啉、咪唑啉、吡咯烷和哌啶系列的空间位阻硝酰基自由基-羟胺以及二芳基羟胺体系中氢原子的直接和反向交换反应的速率常数。建立了水胺还原能力的量表。低同位素效应值是羟胺-硝酰基自由基体系中氢交换反应的典型特征。
• Twisted Diarylnitroxides: An Efficient Route for Radical Stabilization
  作者：Oleg A. Levitskiy、Dmitry B. Eremin、Alexey V. Bogdanov、Tatiana V. Magdesieva

  DOI：10.1002/ejoc.201700947

  日期：2017.9.1

  new twisted diarylnitroxides with tBu and CF3 substituents was obtained. The novel radicals constitute the first examples of stable diarylnitroxides with the vacant para-position in the phenyl ring. This new approach will broaden the scope of available stable and practically important nitroxides.

  在干扰苯环与自由基中心共轭的基础上，提出了稳定的二芳基硝基氧化物分子设计的新策略。获得了一系列具有t Bu和CF 3取代基的新的扭曲的二芳基硝基氧化物。新的基团构成在苯环中具有空位对位的稳定的二芳基硝基氧化物的第一个实例。这种新方法将拓宽可用的稳定且对实际重要的氮氧化物的范围。
• Reductive chlorination of bis(4-tert-butylphenyl)amine-N-oxyl nitroxyl radical
  作者：V. A. Golubev、V. D. Sen’

  DOI：10.1007/s11172-013-0300-1

  日期：2013.9

  Unlike cyclic aliphatic nitroxyls, whose oxidation with halogens gives oxoammonium salts, bis(4-tert-butylphenyl)amine-N-oxyl (1) treated with chlorine undergoes reductive chlorination to the corresponding di- and trichlorodiphenylamines. Chlorine partially dealkylates the compounds obtained. Plausible mechanisms for these reactions were suggested.

  与脂环式硝基羟基化合物不同，后者与卤素发生氧化反应生成氧代铵盐，而双（4-叔丁基苯基）胺-N-羟基（1）与氯发生还原氯化反应生成相应的二氯和三氯二苯胺。氯使所得化合物部分脱烷基化。人们提出了这些反应的可能机理。
• Effect of the chemical structure of nitroxyl radicals on their reactivity in the reaction with hydrazobenzene and tetranitromethane
  作者：A. D. Malievskii、S. V. Koroteev、L. B. Volodarskii、A. B. Shapiro

  DOI：10.1007/bf00958847

  日期：1990.11

  The reaction rate constants of reduction of stable radicals of different classes by hydrazobenzene in hexane at approximately 20-degrees-C, in the range of 0.4-5.10(3) M-1.sec-1, were determined; a single scale of the oxidative properties of stable nitroxyl radicals was constructed. The rate constants of oxidation of a series of nitroxyl radicals by tetranitromethane in aqueous medium at approximately 20-degrees-C, in the range of 0.06-10 M-1.sec-1, were determined. It was shown that the oxidative properties of the nitroxyl group decrease slightly with an increase in its reducing properties for nitroxyl radicals of the piperidine and imidazoline series in reactions with ascorbic acid and tetranitromethane in aqueous medium, respectively.
• Oxidation and reductive bromination of Bis(4-tert-butylphenyl)aminoxyl
  作者：V. A. Golubev、V. D. Sen’

  DOI：10.1134/s1070428013080083

  日期：2013.8

  One-electron oxidation of bis(4-tert-butylphenyl)aminoxyl with antimony pentachloride and bromine leads to the formation of oxoammonium salts with anions SbCl (6) (-) and Br (3) (-) respectively. The salt with the Br (3) (-) anion converted at heating into a mixture of bromodiphenylamines which formed also from the aminoxyl as a result of previously unknown reaction of three-electron reductive bromination. The mechanisms of these reactions were assumed.